Triethylamine → 1-{2-[{6-[(tert-Butoxycarbonyl)amino]hexanoyl}(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate

HRID 446510Notes

Reaction equation

HRID 446510 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[C:31]1([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH:37][C:38](=[O:50])[O:39][CH:40]1[CH2:45][CH2:44][N:43]([CH2:46][CH2:47][NH:48][CH3:49])[CH2:42][CH2:41]1>C(Cl)Cl>[C:31]1([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH:37][C:38](=[O:50])[O:39][CH:40]1[CH2:45][CH2:44][N:43]([CH2:46][CH2:47][N:48]([C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:49])[CH2:42][CH2:41]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 6376026-((tert-Butoxycarbonyl)amino)hexanoic acidHCID 566436031-(2-(Methylamino)ethyl)piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamate

Product 1

HCID 666716851-{2-[{6-[(tert-Butoxycarbonyl)amino]hexanoyl}(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamateYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-[(tert-Butoxycarbonyl)amino]hexanoic acid (720 mg, 3.11 mmol) was dissolved in methylene chloride (14 mL), triethylamine (0.590 mL, 4.25 mmol) and pivaloyl chloride (0.418 mL, 3.40 mmol) were added under ice cooling, and the mixture was stirred at room temperature for 15 minutes. 1-[2-(Methylamino)ethyl]piperidin-4-yl biphenyl-2-ylcarbamate (1.00 g, 2.83 mmol) was added, and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1→4 0:100, v/v) to give the title compound (1.59 g; yield, 99%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by NH silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-43f1e4fbcd174e8c830bbb86e71e6bd0
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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